Phenylpiracetam

Phenylpiracetam
Clinical data
Trade names	Phenotropil, Fenotropil, Phenotropyl, Fenotropyl, Carphedon, Actitropil
Other names	Fonturacetam; Phenotropil; Fenotropil; 4-Phenylpiracetam; PP
Pregnancy; category	Unknown;
Routes of; administration	Oral (tablets)
Drug class	Atypical dopamine reuptake inhibitor
ATC code	None;
Legal status
Legal status	AU: S4 (Prescription only); US: Unapproved drug; use in dietary supplements, food, or medicine is unlawful.; RU: Rx-only;
Pharmacokinetic data
Bioavailability	~100%
Metabolism	Not metabolized
Onset of action	<1 hour
Elimination half-life	3–5 hours
Excretion	Urine: ~40%; Bile, sweat: ~60%
Identifiers
	IUPAC name (R,S)-2-(2-oxo-4-phenylpyrrolidin-1-yl)acetamide;
CAS Number	77472-70-9 ;
PubChem CID	132441;
ChemSpider	116950 ;
UNII	99QW5JU66Y;
CompTox Dashboard (EPA)	DTXSID30868438 ;
ECHA InfoCard	100.214.874
Chemical and physical data
Formula	C12H14N2O2
Molar mass	218.256 g·mol−1
3D model (JSmol)	Interactive image;
Chirality	Racemic mixture
Boiling point	486.4 °C (907.5 °F)
	SMILES C1=CC=CC=C1C2CN(C(C2)=O)CC(=O)N;
	InChI InChI=1S/C12H14N2O2/c13-11(15)8-14-7-10(6-12(14)16)9-4-2-1-3-5-9/h1-5,10H,6-8H2,(H2,13,15) ; Key:LYONXVJRBWWGQO-UHFFFAOYSA-N ;
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Phenylpiracetam, also known as fonturacetam (INNTooltip International nonproprietary name) and sold under the brand names Phenotropil, Actitropil, and Carphedon among others, is a stimulant and nootropic medication used in Russia and certain other Eastern European countries in the treatment of cerebrovascular deficiency, depression, apathy, and attention, and memory problems, among other indications. It is also used in Russian cosmonauts to improve physical, mental, and cognitive abilities. The drug is taken by mouth.

Side effects of phenylpiracetam include sleep disturbances among others. The mechanism of action of phenylpiracetam was originally unknown. However, it was discovered that (R)-phenylpiracetam is a selective atypical dopamine reuptake inhibitor in 2014. In addition, phenylpiracetam interacts with certain nicotinic acetylcholine receptors. Chemically, phenylpiracetam is a racetam and phenethylamine and is structurally related to piracetam.

Phenylpiracetam was first described in 1983 by Bobkov Iu, et al. It was approved for medical use in Russia in 2003. Development of (R)-phenylpiracetam (code name MRZ-9547) in the West as a potential treatment for fatigue related to Parkinson's disease began by 2014.